Hydrochloric Acid → HCID 136038177, compound

HRID 1619415Notes

Reaction equation

HRID 1619415 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.[CH3:16][CH:17]([CH3:21])[CH2:18][C:19]#[N:20].Cl.O>O1CCOCC1>[CH2:18]([C:19]1[NH:20][C:4](=[O:6])[C:3]2[C:2](=[CH:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=2)[N:1]=1)[CH:17]([CH3:21])[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 12244IsovaleronitrileHCID 79336Dimethyl aminoterephthalate

Product 1

HCID 136038177HCID 136038177, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of dimethyl 2-aminoterephthalate (3.0 g, 14.4 mmol), 3-methylbutanenitrile (1.2 g, 14.4 mmol), and saturated HCl solution in dioxane (20 mL) in sealed tube was stirred at 100° C. overnight. After it was cooled to room temperature, the reaction mixture was poured into water (50 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layer was concentrated and the residue was purified by silica gel chromatography give the desired product. MS (ESI): 260 (MH+).

Workup

  1. temperatureAfter it was cooled to room temperature
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. concentrationThe combined organic layer was concentrated
  4. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-254e0a1eee454e64b06c0303fb8954d3
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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